title: Enantioselective α-arylation of aldehydes via the productive merger of iodonium salts and organocatalysis.
abstract: The enantioselective α-arylation of aldehydes has been accomplished using diaryliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable α-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.
authors.affiliation: Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA.
authors.forename: Anna E
authors.initials: AE
authors.lastname: Allen
authors.forename: David W C
authors.initials: DW
authors.lastname: MacMillan
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D006847:Hydrocarbons, Iodinated; D012492:Salts